You’re the top dog. Everyone knows it, even if they haven’t actually seen the HR spreadsheet where your name sits comfortably at the top of the ‘Total Compensation’ column. It’s a weird, lonely place to be. You want more money—because who doesn’t?—but you feel like a bit of a jerk asking for it when you’re already making more than the guy who hired you.
Most advice tells you to ‘look at market rates.’ That is useless for you. You are the market rate. You’ve exceeded it. If you look at Glassdoor or PayScale (which I personally loathe because their data is consistently $15k-$20k off for anyone actually good at their job), you’ll just see that you’re already ‘overpaid’ by their standards. But you aren’t overpaid. You’re just rare.
The awkward truth about being at the ceiling
I remember sitting in a glass-walled conference room in Austin back in 2019. I was pulling $165k as a senior lead, which in that specific office, was the absolute peak. I knew for a fact that the next person down was at $140k. I wanted $185k. When I brought it up to my manager, he looked at me like I’d just asked for a company-funded pony. He literally said, ‘You’re already at the top of the band, man. There’s nowhere else to go.’
I felt like an idiot. I felt greedy. I walked out of that meeting and didn’t bring it up again for six months. That was my mistake. I let the ‘band’ dictate my value rather than my actual output. I was managing three high-priority projects and had personally saved a $2M contract that was about to walk out the door because a junior dev had insulted the client’s CTO. I had the leverage, but I let the ‘ceiling’ scare me off.
What I mean is—actually, let me put it differently: the ceiling is a lie created by people who are scared of their own budgets. Most managers are terrified of their own bosses and will tell you ‘there’s no headroom’ just to avoid a difficult conversation upstairs. It’s not that the money isn’t there. It’s that they don’t want to explain why one person is worth two and a half of everyone else.
Never again.
Why market data is actually garbage
I used to think that showing a manager a printout of ‘average salaries for this role in Chicago’ was a winning move. I was completely wrong. It’s a defensive move, not an offensive one. When you’re already the highest paid, market data is your enemy. It’s the tool the company uses to keep you down. They’ll show you a chart from some corporate consulting firm that says you should be earning $10k less than you currently are.
The ‘market’ is for average people doing average work. If you are the highest paid, you have already opted out of the average. Stop using their tools.
I actively tell my friends to avoid PayScale. I’ve found that their ‘research’ is basically just a collection of self-reported data from people who are unhappy with their pay, which naturally skews the numbers lower. It’s a feedback loop of mediocrity. If you want to negotiate from the top, you have to talk about Replacement Cost.
I once tracked my own output for 14 months. I found that I was closing 42% more tickets than the next most senior person on the team. That’s a specific, hard number. When I went back into a negotiation (this time at a different firm), I didn’t talk about what other companies paid. I talked about the fact that if I left, they would have to hire two people to replace my volume, and those two people would cost them a combined $240k plus benefits. Suddenly, my $20k raise looked like a bargain.
Total lie.
The part nobody talks about (the HR rant)
Here is my raw, probably unfair take: HR is the department of ‘No.’ Their entire job, despite what the ‘People & Culture’ posters say, is to minimize risk and cost. When you ask for a raise that puts you further above the internal ‘band,’ you are creating a ‘statistical outlier’ that makes their reports look messy. They hate that.
I know people will disagree, but I think you should almost entirely bypass HR in these conversations. Talk to the person who actually feels the pain when you aren’t there. HR doesn’t care if the codebase rots or if the client leaves; they care that the compensation ratios stay within a 15% variance. It’s bureaucratic nonsense. If your boss says ‘HR won’t approve it,’ what they’re actually saying is ‘I don’t value you enough to fight HR for you.’ That’s a cold reality to swallow, but it’s the truth.
Anyway, I digress. The point is that you need to make your boss the advocate. You need to give them the bullets to go into that war for you.
How to actually frame the ‘Impossible’ ask
Since you can’t ask for ‘more because the market says so,’ you have to ask for ‘more because the future requires it.’ This section might be a bit rough because it depends on your specific job, but the logic holds.
- The ‘New Responsibility’ Gambit: Don’t just do more of what you’re doing. Propose a shift in your role that justifies a new title or a ‘specialist’ status that doesn’t exist in their current bands.
- The Retention Bonus: If they truly can’t move the base salary because of ‘equity’ (a word they love to weaponize), ask for a massive retention bonus tied to a 12-month milestone.
- The Equity Swap: I might be wrong about this—some people hate private equity—but I’ve had success asking for more shares in exchange for a smaller base increase. It shows you’re ‘all in,’ which managers love to hear.
Negotiating at the top is like trying to convince a casino to give you a discount on the buffet after you’ve already cleared out the craps table. You have to prove that your presence at the table is what keeps the lights on.
I’ve bought the same $120 notebook for every job I’ve had since 2014. I write down every win, every time I saved a project, and every time I mentored someone who then got promoted. That notebook is my leverage. When I’m the highest paid, I don’t walk in with a ‘request.’ I walk in with a business case for why keeping me happy is the highest ROI decision they will make this year.
Worth every penny.
Is the money even the point?
I’m going to be honest: sometimes you hit a wall that actually is a wall. I’ve been at companies where the CEO literally didn’t make much more than I did. At that point, you aren’t negotiating salary anymore; you’re negotiating for your exit. If you’re the highest paid and you’re still miserable or feeling undervalued, no amount of ‘band-breaking’ is going to fix the fact that you’ve outgrown the pond.
I used to think loyalty was a virtue in tech. I was wrong. Loyalty is often just a fancy word for ‘settling.’ If you are at the top and they won’t budge, the only way to get a raise is to change the room you’re standing in.
It’s a scary thought. Leaving the comfort of being the top earner to go somewhere else where you might just be ‘average’ again. But that’s how you keep growing.
Do you actually like your job, or do you just like being the person who makes the most? I still haven’t figured out the answer to that one for myself.
Go ask for the money. Worst they can say is no.